Literature DB >> 19199662

Catalytic intermolecular aldehyde-ketone coupling via acyl phosphonates.

Ayhan S Demir1, Lker Esiringü, Mehmet Göllü, Omer Reis.   

Abstract

The first catalytic intermolecular aldehyde-ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41-95% yields.

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Year:  2009        PMID: 19199662     DOI: 10.1021/jo8026627

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates.

Authors:  Michael T Corbett; Daisuke Uraguchi; Takashi Ooi; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

3.  Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions and kinetic resolution of resultant alpha-silyloxyketones.

Authors:  James C Tarr; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

4.  Validation of diethoxyphosphonate as an effective agent for charge transfer in Anion Relay Chemistry (ARC).

Authors:  Alexander Sokolsky; Amos B Smith
Journal:  Org Lett       Date:  2012-08-10       Impact factor: 6.005

5.  Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions.

Authors:  James C Tarr; Jeffrey S Johnson
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

6.  Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitrostyrenes.

Authors:  Somayeh Motevalli; Jeffrey S Johnson
Journal:  Synthesis (Stuttg)       Date:  2017-05-02       Impact factor: 3.157

7.  Synthesis of dinucleoside acylphosphonites by phosphonodiamidite chemistry and investigation of phosphorus epimerization.

Authors:  William H Hersh
Journal:  Beilstein J Org Chem       Date:  2015-01-30       Impact factor: 2.883

  7 in total

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